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Chapter 11 - Chapter 11. The Chemistry of Ethers,...

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Unformatted text preview: Chapter 11. The Chemistry of Ethers, Epoxides, Glycols, and Sulfides Ethers, epoxides, glycols, and sulfides Ether: less reac?ve than other types of compounds. Epoxides: a heterocyclic ether; very reac?ve. Glycols (diols), related to alcohols and epoxides. Thioethers (sulfides) are sulfur analogs of ethers just as thiols are from alcohols. Williamson ether synthesis Alexander W. Williamson FRS (1 May 1824 – 6 May 1904) Alkoxymercura?on ­reduc?on of alkenes Alcohol dehydra?on Ether from alkene addi?on Synthesis of epoxides Hydroperoxy group Fic??ous step ­wise mechanism Concerted mechanism How do you know that the epoxida?on is a concerted process? Syn ­addi?on Cycliza?on of halodrins Epoxide chemistry: ring ­opening Basic condi?ons Epoxide chemistry: ring ­opening Acidic condi?on Epoxide chemistry: Ring ­Opening Reac?on with organometallic reagents Cleavage of ethers Ter?ary ether cleavage Oxida?ve cleavage of glycols Prepara?on of glycols Neighboring group par?cipa?on Proximity effect Neighboring ­group par?cipa?on accelerates the SN2 reac?on Stereochemical consequences? •  Func?onal groups in ether, epoxides, glycols, and sulfides. Their physical and chemical characteris?cs; •  Williamson ether synthesis (reagents, condi?ons, and mechanisms); •  Ether cleavage (SN2 and SN1 mechanism for primary and ter?ary ether); •  Ring opening reac?ons under acidic and basic condi?ons (mechanism, product distribu?on, stereochemistry); •  Epoxide ring opening with Grignard reagents and applica?on; •  Applica?on of using organo ­lithium and –copper reagents in synthesis; •  Prepara?on and oxida?ve cleavage of glycols; •  Neighboring ­group par?cipa?on and proximity effect (applica?on, mechanism, stereochemistry) Key Points Homework and Reading Assignment •  12/7 Reading assignment: 482  ­ 495 Homework: 11.2,11.5,11.8,11.9,11.12,11.14,11.15, 11.1,11.6,11.10, 11.11,11.16, 11.46, 11.47 •  12/9 Reading assignment: 495  ­ 527 Homework: 11.17, 11.18, 11.19, 11.21, 11.22, 11.25, 11.27, 11.35, 11.35, 11.38, 11.39, 11.41, 11.44, 11.60, 11.74, 11.75, 11.76, 11.78 •  12/11 Reading assignment: None Homework: None ...
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